Design and Construction
At 56 feet 3 inches overall with a 45-foot-6-inch waterline and a 15-foot-9-inch beam, the 55 carries 51,000 pounds of displacement on a modified fin keel and skeg-hung rudder, with a canoe underbody and an optional high-performance bulb or Scheel keel available to buyers who wanted different grounding characteristics. The hull itself drew an average score of 10 for construction in reader surveys, with bulkheads and the hull/deck joint rated perfect 10s and chainplates likewise faultless; the balsa-cored deck sat a point lower at 9, while stringers and floors averaged 8 and exterior stainless a more modest 7. A well-insulated engine compartment sits under the center-cockpit, spacious enough to swallow a generator, and the deck saloon arrangement gives the boat its long-waterline, volume-rich profile.
Rig and Handling
Every Oyster 55 is a saloon-deck cutter, with almost all carrying furling headsails and staysails plus in-mast furling mains — typically a Hood Stoway spar paired with Hood headsail-furling systems for both yankee and staysail. Only three were built as ketches, the rest sloops. The tall rig drives a large sail area of 1,672 square feet with a 150 percent headsail, sitting on a Displacement/Length ratio of 242 and a Sail Area/Displacement ratio of 19.5. Under power, an 82-horsepower Perkins with a three-bladed feathering Max Prop is typical, turned through a Whitlock Premier steering pedestal. Reader surveys scored her motion in a seaway a 9, deck safety and reefing setup likewise 9, and watertightness below decks a 9; light-air and upwind work drew only 7s, but moderate breeze through storm conditions scored between 9 and 10, and downwind running a 9.
Accommodations
The raised saloon, an Andrew Winch design, is built around a curved settee to starboard and a loveseat to port, with a teak and holly sole under teak joinery that survey respondents rated a perfect 10 for cabinetry. True upper and lower sea berths lie to starboard just forward of the dinette and to port just aft of the companionway, while the aft cabin holds a double berth and two heads serve the plan. The nav-station to port of the companionway scored between 9 and 10, and the galley — four-burner gas range, refrigerator/freezer, double sinks — rated an average 8 as a seagoing tool with 8.5 for storage and 9 overall efficiency. The saloon table was deemed a perfect 10, and the below-deck plan for living aboard an uncompromising 10, though sea-berth quality averaged only 7 to 8 and wet-gear stowage a lone 7.
Performance and Rally Record
This is a design with a competitive streak. Oyster 55 successes include twice topping the points table at Antigua Race Week — the boat Flying Scotsman took the overall cruising division there twice — plus ARC class wins and Europa Rally successes. She is the single most prolific boat choice for the Trade Winds Round the World Rally, with seven examples having taken part, a testament to the short-handed bluewater remit Holman & Pyle were given.
Ownership and Refits
Because each hull was semi-custom, owners specified wood species, layout count (three or four cabins), and equipment levels individually. Many carry electric drive and electric primary winches, almost all are fitted with Perkins 4236 84-horsepower diesels and Westerbeke generators, and a self-draining life raft locker in the aft deck plus a capacious lazarette round out the practical cruising provisions. The readership's overall offshore rating landed at 9.5, with cockpit protection between 8 and 9 and dryness on deck an 8.
The Verdict
The Oyster 55 is a heavily built, thoughtfully laid-out bluewater cutter whose semi-custom origins let each owner tailor the interior without compromising a structurally impeccable hull. She rewards a short-handed crew with manageable furling rigs and strong moderate-to-heavy-air performance, though light-air and upwind numbers show the limits of her displacement.
Pros
- Impeccable hull, bulkhead, and chainplate construction per owner surveys
- Deck-saloon volume with a living-aboard plan rated perfect by readers
- Proven short-handed rally and race record including Trade Winds Round the World
- Semi-custom interiors in owner-chosen wood and three- or four-cabin layouts
Cons
- Light-air and upwind performance scored only 7 in reader surveys
- Sea-berth quality and wet-gear stowage rated relatively low (7 to 8)
- Exterior stainless averaged a 7, a weak point against otherwise flawless structure
